WO2002100368A1 - Composition pour la teinture des fibres keratiniques comprenant un colorant diazo'ique dicationique particulier - Google Patents

Composition pour la teinture des fibres keratiniques comprenant un colorant diazo'ique dicationique particulier Download PDF

Info

Publication number
WO2002100368A1
WO2002100368A1 PCT/FR2002/001990 FR0201990W WO02100368A1 WO 2002100368 A1 WO2002100368 A1 WO 2002100368A1 FR 0201990 W FR0201990 W FR 0201990W WO 02100368 A1 WO02100368 A1 WO 02100368A1
Authority
WO
WIPO (PCT)
Prior art keywords
ium
radical
dimethyl
methyl
ylazo
Prior art date
Application number
PCT/FR2002/001990
Other languages
English (en)
French (fr)
Inventor
Laurent Vidal
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to EP02760357A priority Critical patent/EP1399117B1/fr
Priority to KR10-2003-7016170A priority patent/KR20040003065A/ko
Priority to MXPA03011393A priority patent/MXPA03011393A/es
Priority to BR0210997-2A priority patent/BR0210997A/pt
Priority to DE60215808T priority patent/DE60215808T2/de
Priority to JP2003503192A priority patent/JP2005516887A/ja
Priority to US10/480,153 priority patent/US6893471B2/en
Publication of WO2002100368A1 publication Critical patent/WO2002100368A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/12—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom
    • C09B44/126—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom in a six-membered ring, e.g. pyrridinium, quinolinium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/18—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having three nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/20—Thiazoles or hydrogenated thiazoles

Definitions

  • the subject of the invention is a new dye composition for dyeing keratin fibers, in particular human keratin fibers and more particularly hair, comprising a particular dicationic diazo dye, as well as the process for dyeing keratin fibers using such a dye.
  • Another subject of the invention is new diazo dicationic dyes. It is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, generally called oxidation bases, such as ortho or para-phenylenediamines, ortho or paraaminophenols and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, give rise, through an oxidative condensation process, to colored compounds.
  • couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as indole compounds.
  • This oxidation dyeing process consists in applying to the keratin fibers, oxidation bases or a mixture of oxidation bases and couplers with an oxidizing agent, for example hydrogen peroxide, to leave on, then to rinse the fibers.
  • the resulting colorings are permanent, powerful, and resistant to external agents, in particular to light, bad weather, washing, perspiration and rubbing.
  • Generally applied at basic pH it makes it possible to obtain a dyeing and at the same time a lightening of the fiber which translates in practice by the possibility of obtaining a final coloration lighter than the original color.
  • the lightening of the fiber has the advantageous effect of generating a solid color in the case of gray hair, and in the case of naturally pigmented hair, of bringing out the.
  • direct dyeing consists in applying to the keratin fibers direct dyes which are colored and coloring molecules having an affinity for the fibers, to allow to pause, then to rinse the fibers. It is known, for example, to use direct dyes belonging to the class of benzene nitrates, anthraquinones, nitropyridines, azo, indoamines, azines or triarylmethanes.
  • the resulting colorings are particularly chromatic colors which are however temporary or semi-permanent because the nature of the interactions which bind the direct dyes to the keratin fiber, and their desorption from the surface and / or from the core of the fiber are responsible for their low dye power and their poor resistance to washing or perspiration.
  • These direct dyes are also generally sensitive to light due to the low resistance of the chromophore vis-à-vis photochemical attacks and lead over time to a fading of the coloring of the hair. In addition, their sensitivity to light is dependent on their uniform or aggregate distribution in the keratin fiber.
  • direct dyes are generally sensitive to the action of oxidizing agents such as hydrogen peroxide, and reducing agents such as sodium bisulfite, which makes them generally difficult to use in lightening direct dye compositions based on hydrogen peroxide and based on an alkalizing agent or in oxidation dye compositions in combination with precursors of the oxidation base or coupler type.
  • oxidizing agents such as hydrogen peroxide
  • reducing agents such as sodium bisulfite
  • patent application FR 2 741 798 has described dye compositions containing direct dyes comprising at least one quaternized nitrogen atom of the azo or azomethine type, said compositions being to be mixed extemporaneously at basic pH with an oxidizing composition.
  • These compositions make it possible to obtain colorings with homogeneous, tenacious and brilliant reflections. However, they do not make it possible to dye the keratin fibers with as much power as with oxidation coloring compositions.
  • composition for dyeing keratin fibers in particular human keratin fibers and more particularly hair, comprising at least one diazo dicationic dye of formula (I) below:
  • W 2 represents a carbon, pyridine or pyridazinyl aromatic group of formula (IV)
  • - -i represents a nitrogen atom or a radical CR 5
  • - X 2 represents a nitrogen atom or a radical CR 6
  • Z t represents an oxygen or sulfur atom or an NR 8 radical
  • - Z 2 represents a nitrogen atom or a CR 9 radical
  • - Z 3 represents a nitrogen atom or a CR 12 radical
  • Z 4 represents a nitrogen atom or a CR 13 radical
  • R 3 , R, R5, Re, R7, R9, Rio, R11, R12, 13 > represent, together or independently of one another, a hydrogen atom, a linear or branched CC 16 hydrocarbon chain , saturated or unsaturated, possibly form one or more carbon rings comprising from 3 to 6 members, one or more carbon atoms of the carbon chain of which can be replaced by an oxygen, nitrogen or sulfur atom or by an SO 2 group, and the carbon atoms can be, independently of one another, substituted by one or more halogen atoms; R 3 , R 4 , R5, Re, R7, Rg, R10, Ru, R12, R13, comprising no peroxide bond, nor diazo or nitroso radicals, - R 7 with R g , R10 with Ru and R 12 with R ⁇ 3 can form a carbonaceous aromatic ring, such as a phenyl, X is an organic or inorganic anion.
  • branched hydrocarbon chain means a chain which can form one or more carbon rings comprising from 3 to 6 members.
  • unsaturated hydrocarbon chain is understood to mean a chain which can comprise one or more double bonds and / or one or more triple bonds, this hydrocarbon chain being able to lead to aromatic groups.
  • X is an organic or inorganic anion, for example chosen from a halide such as chloride, bromide, fluoride, iodide; a hydroxide; a sulfate; a hydrogen sulfate; an alkyl (CC 6 ) sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; an alkyl (CC 6 ) sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a C 1 -C 4 alkyl radical such as for example a 4-toluylsulfonate.
  • a halide such as chloride, bromide, fluoride, iodide
  • a hydroxide such as a sulfate; a hydrogen sulfate
  • R3, R 4 , R5, Rs, R10, R11, R12, R13 preferably represent, independently of one another, a hydrogen atom; a linear or branched CC alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di) alkylamino CC 2 , carboxy or sulfonic; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) hydroxy C 2 -C alkoxy, amino, (di) alkylamino CC 2 , carboxy, sulfonic or an atom halogen such as chlorine, fluorine or bromine; a carboxy radical; a sulfonylamino radical; a sulfonic radical; a C1-C2 alkoxy radical; a C 2 -C 4 (poly)
  • R 3 , R 4 , R 5 , R 6 , R10, Ru, R 12 , 13 represent a hydrogen atom, a CC 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino radicals , (di) C -, - C 2 alkylamino; a carboxy radical; a CC 2 alkoxy radical; an amino radical; a CC 2 (di) alkylamino radical; a C 2 -C 4 (poly) hydroxyalkylamino radical, according to a particularly preferred embodiment, R 3 , R 4 , R 5 , R 6, R 10 ,
  • R11, R12, R13 represent a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, a carboxy, a methoxy, ethoxy, 2-hydroxyethyloxy radical, an amino, methylamino, dimethylamino, 2-hydroxyethylamino radical.
  • R 7 and R 9 represent, independently of one another, a hydrogen atom; a linear or branched CC 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) hydroxy C 2 -C alkoxy, amino, (di) alkylamino CC 2 , carboxy radicals or sulfonic; an optionally substituted phenyl radical; a carboxy radical; a sulfonylamino radical.
  • R 7 and R 9 preferably represent a hydrogen atom, a phenyl radical, a C r C alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino, (di) alkylamino radicals CC 2 , carboxy.
  • R 7 and R 9 preferably represent a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, a carboxy.
  • Ri, R 2 and R 8 represent an alkyl radical CC 8 linear or branched, optionally substituted by one or more radicals chosen from hydroxyl, alkoxy, C 2 -C (poly) hydroxyalkoxy 'C 2 -C 4 , amino, (di) alkylamino CC 2 , carboxy or sulfonic; an optionally substituted phenyl radical.
  • R ⁇ R 2 and R 8 preferably represents an alkyl radical in CC 4 optionally substituted by one or more radicals chosen from hydroxy, alkoxy in CC 2 , amino, (di) alkylamino in CC 2 , carboxy, sulfonic radicals .
  • R ⁇ R 2 and R 8 preferably represents a methyl, ethyl, 2-hydroxyethyl, 1-carboxymethyl, 2-carboxyethyl, 2-sulfonylethyl radical.
  • Wi and W 3 preferably represent, independently of one another, a cationic group imidazolium, triazolium, thiazolium, pyridinium substituted by the preferred radicals R ⁇ R 7 R 10 , Ru, R ⁇ 2 , R 13 .
  • W 2 preferably represents a phenyl or pyridyl group substituted by the preferred radicals R 3 , R 4 R s , R 6 .
  • the concentration of diazo diazo dye of formula (I) can vary from 0.001 to 5% by weight approximately relative to the total weight of the dye composition, and preferably from approximately 0.05 to 2%.
  • diazo dicationic dyes of formula (I) according to the present invention, mention may in particular be made of the following compounds:
  • a first principle of synthesis consists in reacting a cationic heterocyclic azo on one of the nitrogen atoms of the heterocycle in 4-methoxyphenylazo series with a 5- or 6-membered heterocyclic hydrazone derivative 2 or 2 in a protic solvent at a temperature between 25 ° C and 150 ° C. Compounds 3 and 3 ⁇ can thus be obtained.
  • the quarternary heterocycle can be an imidazolium, triazolium, thiazolium, thiadiazolium, oxazolium, a pyridinium or a pyridazinium.
  • Compounds 3 or 3 ⁇ are reacted with an oxidant, such as for example oxygen, persalts (for example persulfate), potassium ferrocyanide or also silver oxide, in a protic solvent at a temperature between 0 ° C and 80 ° C, to lead to the dicationic diazo compounds 4 and 4 ':
  • a second synthetic principle consists in reacting a 5-membered heterocycle such as an imidazole, thiazole, thiadiazole, triazole or oxazole on the diazonium salt derived from azoic 5 (respectively 9, obtained according to the conventional methods of literature, see references cited above) at a temperature between -5 ° C and 50 ° C, in a protic solvent and at acidic pH.
  • the diazo compound 7 (respectively 10) is thus obtained and reacted with an alkyl halide or a dialkyl sulphate in a solvent with a boiling point of between 60 ° C. and 180 ° C. to yield the diazo compound dicationic 4 (respectively 11.):
  • Me denotes a CH3 radical.
  • the dye composition in accordance with the invention may also contain direct dyes different from those of formula (I), these dyes being able in particular to be chosen from neutral benzenic direct dyes, acid or cationic, neutral azo direct dyes which are acidic or cationic , quinone direct dyes and in particular neutral, acidic or cationic anthraquinone dyes, azine direct dyes, methine direct dyes, triarylmethane direct dyes, indoamine direct dyes and natural direct dyes.
  • direct dyes different from those of formula (I) these dyes being able in particular to be chosen from neutral benzenic direct dyes, acid or cationic, neutral azo direct dyes which are acidic or cationic , quinone direct dyes and in particular neutral, acidic or cationic anthraquinone dyes, azine direct dyes, methine direct dyes, triarylmethane direct dyes, indoamine direct dyes and natural direct dyes.
  • benzenic direct dyes which can be used according to the invention, there may be mentioned in particular the following compounds: -1, 4-diamino-2-nitrobenzene
  • the following dyes may very particularly be mentioned: -3.3-dimethyl-2 chloride - [[4- (dimethylamino) phenyl] azo] -1 H-lmidazolium, -1, 3-dimethyl-2 chloride - [(4-aminophenyl) azo] -1 H-lmidazolium, - 1-methyl-4-methylsulfate - [(methylphenylhydrazono) methyl] -pyridinium.
  • the following dyes may be mentioned: -Disperse Red 15 -Solvent Violet 13 -Acid Violet 43 -Disperse Violet 1 -Disperse Violet 4 -Disperse Blue 1
  • azine dyes the following compounds may be mentioned: -Basic Blue 17 -Basic Red 2.
  • triarylmethane dyes which can be used according to the invention, mention may be made of the following compounds:
  • indoamine dyes which can be used according to the invention, mention may be made of the following compounds: -2- ⁇ -hydroxyethlyamino-5- [bis- ( ⁇ -4'-hydroxyethyl) amino] anilino-1,4-benzoquinone -2- ⁇ -hydroxyethylamino-5- (2'-methoxy-4'-amino) anilino -1,4-benzoquinone -3-N (2'-Chloro-4'-hydroxy) phenyl-acetylamino-6-methoxy-1,4-benzoquinone imine -3-N (3'-Chloro-4'-methylamino) phenyl-ureido-6-methyl-1,4-benzoquinone imine -3- [4'-N- (Ethyl, carbamylmethyl) -amino] -phenyl-ureido-6-methyl-1,4-benzoquinone imine.
  • the additional direct dye (s) preferably represent from 0.001 to 20% by weight approximately of the total weight of the composition and even more preferably from 0.005 to 10% by weight approximately.
  • the composition of the invention may also comprise an oxidizing agent.
  • This oxidizing agent can be any oxidizing agent conventionally used for bleaching keratin fibers.
  • the oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and enzymes among which may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases.
  • the use of hydrogen peroxide is particularly preferred.
  • composition according to the invention can also comprise an oxidation base.
  • This oxidation base can be chosen from the oxidation bases conventionally used in oxidation dyeing, for example paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • paraphenylenediamines there may be more particularly mentioned by way of example, paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine , 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ - hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline , 2- ⁇ -hydroxyethyl
  • paraphenylenediamine paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxyoxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2- ⁇ -acetylaminoethyloxy para-phenylenediamine, and their addition salts with an acid are particularly preferred .
  • the bis-phenylalkylenediamines there may be mentioned by way of example, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3-diamino propanol, N , N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N ' -bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis- (2,
  • para-aminophenol there may be mentioned by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4- amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
  • para-aminophenol 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4- amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
  • ortho-aminophenols there may be mentioned by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
  • heterocyclic bases by way of example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino 6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
  • pyrimidine derivatives mention may be made of the compounds described for example in patents DE 2,359,399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetra-aminopyrim ⁇ iine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which may be mentioned pyrazolo - [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3
  • composition according to the invention may also contain one or more couplers conventionally used for dyeing keratin fibers.
  • couplers conventionally used for dyeing keratin fibers.
  • couplers mention may in particular be made of metaphenylenediamines, metaaminophenols, metadiphenols, naphthalene couplers and heterocyclic couplers.
  • the coupler (s) are generally present in an amount ranging from 0.001 to 10% by weight approximately of the total weight of the dye composition and more preferably from 0.005 to 6%.
  • the oxidation base (s) are present in an amount preferably ranging from
  • the addition salts with an acid which can be used in the context of the dye compositions of the invention for the oxidation bases and the couplers are in particular chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the medium suitable for dyeing also called dye support, generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
  • organic solvent mention may, for example, be made of lower CrC alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the organic solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
  • the dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic polymers, cationic, non-ionic, amphoteric, zwitterionic or mixtures thereof, mineral or organic thickening agents, and in particular associative polymers anionic, cationic, nonionic and amphoteric, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example volatile or non-volatile silicones, modified or not modified, film-forming agents, ceramides, preserving agents, opacifying agents.
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic polymers, cationic, non-ionic, amphoteric,
  • the adjuvants mentioned above are generally present in an amount for each of them of between 0.01 and 20% by weight relative to the weight of the composition.
  • the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers or even with the aid of conventional buffer systems.
  • acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
  • mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
  • basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (III) below:
  • the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
  • the invention also relates to a direct dyeing process which comprises the application of a dye composition containing a dye of formula (I) as defined above on keratin fibers. After a pause, the keratin fibers are rinsed, revealing colored fibers.
  • the application to the fibers of the dye composition containing the azo cationic dye of formula (I) can be used in the presence of an oxidizing agent which causes discoloration of the fiber (direct lightening dye). This oxidizing agent can be added to the composition containing the dye of formula (I) at the time of use or directly on the keratin fiber.
  • the invention also relates to an oxidation dyeing process which comprises applying to the fibers a dye composition which comprises a dye of formula (I), at least one oxidation base and optionally at least one coupler , in the presence of an oxidizing agent.
  • the oxidation base, the coupler and the oxidizing agent are as defined above.
  • the color can be revealed at acidic, neutral or alkaline pH and the oxidizing agent can be added to the composition of the invention just at the time of use or it can be used from an oxidizing composition containing it , applied to the fibers simultaneously or sequentially to the dye composition.
  • the dye composition is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, at least one oxidizing agent, this oxidizing agent being present in an amount sufficient to develop a coloration.
  • the mixture obtained is then applied to the keratin fibers.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 11 It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above.
  • the composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratin fibers, and in particular human hair.
  • Another object of the invention is a device with several compartments or "kit” for dyeing in which a first compartment contains the dye composition of the invention and a second compartment contains the oxidizing composition.
  • This device can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2586 913 in the name of the applicant. '
  • the subject of the invention is also the diazo dicaton dyes of formula (I) as defined above.
  • the dye obtained dyed the hair in a purple shade.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/FR2002/001990 2001-06-11 2002-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazo'ique dicationique particulier WO2002100368A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP02760357A EP1399117B1 (fr) 2001-06-11 2002-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazoïque dicationique particulier
KR10-2003-7016170A KR20040003065A (ko) 2001-06-11 2002-06-11 특정 2양이온성 디아조 염료를 함유하는 케라틴 섬유염색용 조성물
MXPA03011393A MXPA03011393A (es) 2001-06-11 2002-06-11 Composicion para tenido de fibras queratinicas que comprende colorante diazoico dicationico particular.
BR0210997-2A BR0210997A (pt) 2001-06-11 2002-06-11 Composição e processo para a tintura das fibras queratìnicas, processo de tintura de oxidação das fibras queratìnicas, dispositivo ou " kit" de tintura com vários compartimentos e compostos diazóicos dicatiÈnicos
DE60215808T DE60215808T2 (de) 2001-06-11 2002-06-11 Eine dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
JP2003503192A JP2005516887A (ja) 2001-06-11 2002-06-11 特定の二価陽イオン性ジアゾ染料を含むケラチン繊維用の染色組成物
US10/480,153 US6893471B2 (en) 2001-06-11 2002-06-11 Dyeing composition for keratinous fibers comprising a particular dicationic diazo dye

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR01/07614 2001-06-11
FR0107614A FR2825702B1 (fr) 2001-06-11 2001-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique diazoique dicationique particulier

Publications (1)

Publication Number Publication Date
WO2002100368A1 true WO2002100368A1 (fr) 2002-12-19

Family

ID=8864177

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2002/001990 WO2002100368A1 (fr) 2001-06-11 2002-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazo'ique dicationique particulier

Country Status (13)

Country Link
US (1) US6893471B2 (es)
EP (1) EP1399117B1 (es)
JP (1) JP2005516887A (es)
KR (1) KR20040003065A (es)
CN (1) CN1277528C (es)
AT (1) ATE344090T1 (es)
BR (1) BR0210997A (es)
DE (1) DE60215808T2 (es)
ES (1) ES2274077T3 (es)
FR (1) FR2825702B1 (es)
MX (1) MXPA03011393A (es)
PT (1) PT1399117E (es)
WO (1) WO2002100368A1 (es)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006056489A2 (en) * 2004-11-26 2006-06-01 L'oreal Particular dissymmetrical cationic polyazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibres and device therefor
FR2879190A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques presentant au moins un motif 4-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
FR2879197A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 3-pyridinium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif
FR2879193A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques presentant au moins un motif 2-imidazolium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
FR2879198A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 3-pyridium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif
FR2879191A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques particuliers et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
FR2879195A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
WO2006063869A2 (en) * 2004-12-15 2006-06-22 L'oreal Symmetrical diazo compounds with 3-pyridinium groups and cationic linker arm, compositions comprising same, dyeing method and device
WO2006063867A2 (en) * 2004-12-15 2006-06-22 L'oréal Symmetrical diazo compounds containing 3-pyridinium groups and a non-cationic linker, compositions comrisisng them, method of colouring, and device
JP2006525977A (ja) * 2003-05-09 2006-11-16 ロレアル 熱を加えることによりケラチン繊維をトリートメントするための方法
JP2006348264A (ja) * 2004-10-14 2006-12-28 L'oreal Sa ジカチオンビス−ヒドラゾン化合物、少なくとも一種のこのような化合物を含む染料組成物、その実施方法及びその使用
US7247713B2 (en) 2004-12-15 2007-07-24 L'oreal, S.A. Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device
US7288639B2 (en) 2004-12-15 2007-10-30 L'oreal S.A. Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device
US7351267B2 (en) 2004-12-15 2008-04-01 L'oreal S.A. Symmetrical diazo compounds comprising 2-imidazolium groups and a non-cationic linke, compositions comprising them, method of coloring, and device
US7396368B2 (en) 2004-12-15 2008-07-08 L'oreal S.A. Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device
US7438728B2 (en) 2004-12-15 2008-10-21 L'oreal S.A. Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device

Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2841901B1 (fr) * 2002-07-05 2006-02-03 Oreal Utilisation d'un compose tetraazapentamethinique en tant que colorant direct et nouveaux composes tetraazapentamethiniques
US7169194B2 (en) 2002-12-23 2007-01-30 L'oreal S.A. Dye composition comprising at least one particular tricationic direct dye, dyeing process, use and multi-compartment devices
FR2848838B1 (fr) * 2002-12-23 2005-03-11 Oreal Composition tinctoriale contenant un colorant direct tricationique, particullier, procede de teinture, utilisation et dispositifs a plusieurs compartiments.
US20050235432A1 (en) * 2004-01-28 2005-10-27 Gregory Plos Composition for dyeing keratin fibers, comprising at least one alcohol oxidase, at least one oxidation dye precursor, and at least one azo, methine or azomethine cationic direct dye, and process using this composition
US7410506B2 (en) 2004-10-14 2008-08-12 L'oreal S.A. Dicationic bis-hydrazone compound, dye composition comprising at least one such compound, implementation process therefor and uses thereof
US20060130244A1 (en) * 2004-11-25 2006-06-22 Franck Giroud Aqueous composition for dyeing keratin fibres comprising a dye and a specific block copolymer
FR2878154B1 (fr) 2004-11-25 2007-02-09 Oreal Composition aqueuse de coloration des fibres keratiniques comprenant un colorant et un copolymere blocs particulier
FR2879199B1 (fr) 2004-12-15 2007-02-02 Oreal Composes diazoiques symetriques a groupements 2-imidazolium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif
FR2879192B1 (fr) 2004-12-15 2007-02-02 Oreal Composes diazoiques dissymetriques a groupement 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
FR2879200B1 (fr) 2004-12-15 2007-02-02 Oreal Composes diazoiques symetriques a groupements 4-pyridium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
US20090062517A2 (en) * 2004-12-15 2009-03-05 L'oreal S.A. Dissymmetrical Diazo Compounds Containing Having at Least One 2-imidazolium Unit and a Cationic or Non-cationic Linker, Compositions Comprising Them, Method of Coloring, and Device
US7429275B2 (en) * 2004-12-23 2008-09-30 L'oreal S.A. Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor
FR2882518B1 (fr) 2005-02-28 2012-10-19 Oreal Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct anthraquinonique, composition comprenant ledit colorant et son procede de preparation
US20060236469A1 (en) * 2005-02-28 2006-10-26 Eric Bone Anhydrous composition in the form of a film comprising a film-forming polymer and oxidizing agent, preparation and process for coloring keratinous fibers employing the anhydrous composition
FR2882519B1 (fr) 2005-02-28 2008-12-26 Oreal Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct azomethinique composition comprenant ledit colorant et son procede de preparation
FR2882560B1 (fr) 2005-02-28 2007-05-18 Oreal Composition anhydre sous forme de film comprenant un polymere filmogene et un colorant d'oxydation, preparation et procede de coloration la mettant en oeuvre
FR2882561B1 (fr) 2005-02-28 2007-09-07 Oreal Composition anhydre sous forme de film comprenant un polymere filmogene et un colorant direct, preparation et procede de coloration la mettant en oeuvre
FR2882559B1 (fr) 2005-02-28 2008-03-21 Oreal Composition anhydre sous forme de film comprenant un polymere filmogene et un agent oxydant, preparation et procede de traitement de fibres keratiniques la mettant en oeuvre
FR2882521B1 (fr) 2005-02-28 2008-05-09 Oreal Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct, composition comprenant ledit colorant et son procede de preparation
US20060242771A1 (en) * 2005-02-28 2006-11-02 Eric Bone Anhydrous composition in the form of a film comprising a film-forming polymer and a direct dye, preparation and dyeing process using the composition
US20060230546A1 (en) * 2005-02-28 2006-10-19 Eric Bone Anhydrous composition in the form of a film comprising at least one film-forming polymer and at least one oxidation dye, preparation, and dyeing process
FR2883736B1 (fr) 2005-03-31 2007-05-25 Oreal Composition colorante comprenant un ester d'acide gras et procede de coloration de fibres keratiniques la mettant en oeuvre
FR2883738B1 (fr) 2005-03-31 2007-05-18 Oreal Composition colorante comprenant un polymere associatif non ionique, procede de coloration de fibres keratiniques la mettant en oeuvre
US7575605B2 (en) * 2005-03-31 2009-08-18 L'oreal S.A. Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition
US7651533B2 (en) 2005-03-31 2010-01-26 Oreal Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor
FR2883746B1 (fr) 2005-03-31 2007-05-25 Oreal Composition colorante comprenant une cellulose et procede de coloration de fibres keratiniques la mettant en oeuvre
US7569078B2 (en) * 2005-03-31 2009-08-04 L'oreal S.A. Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition
US7550015B2 (en) * 2005-03-31 2009-06-23 L'oreal S.A. Dye composition with a reduced content of starting materials, and process for dyeing keratin fibers using the same
FR2883734B1 (fr) 2005-03-31 2007-09-07 Oreal Composition colorante a teneur diminuee en matieres premieres et procede de coloration de fibres keratiniques la mettant en oeuvre
FR2883737B1 (fr) 2005-03-31 2009-06-12 Oreal Composition colorante comprenant un ester de glyceryle et procede de coloration de fibres keratiniques la mettant en oeuvre
FR2883735B1 (fr) 2005-03-31 2009-06-12 Oreal Composition colorante a teneur diminuee en matieres premieres, procede de coloration de fibres keratiniques la mettant en oeuvre et dispositif
US7578854B2 (en) * 2005-03-31 2009-08-25 L'oreal S.A. Dye composition comprising at least one fatty acid ester and process for dyeing keratin fibers using the same
US7442214B2 (en) * 2005-03-31 2008-10-28 L'oreal S.A. Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same
FR2885045B1 (fr) 2005-04-29 2007-06-08 Oreal Emulsion inverse comprenant une solution de peroxyde d'hydrogene et une phase inerte de solubilite dans l'eau inferieure a 1%
US7485156B2 (en) 2005-05-31 2009-02-03 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler and at least one associative polyurethane polymer
US7488356B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one surfactant
US7582121B2 (en) 2005-05-31 2009-09-01 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
US7488355B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising a diamino-N,N-dihydropyrazolone compound, a coupler, and a polyol
US7497878B2 (en) 2005-06-30 2009-03-03 L'oreal, S.A. Azo dyes containing a sulphonamide or amide function for the dyeing of human keratin fibers and method of dyeing and dyeing compositions containing them
US7905925B2 (en) 2005-08-25 2011-03-15 L'oreal S.A. Dye composition comprising at least one insoluble compound and processes using this composition
FR2889944B1 (fr) 2005-08-25 2007-11-23 Oreal Composition tinctoriale comprenant des composes insolubles, procedes mettant en oeuvre cette composition.
FR2889947B1 (fr) 2005-08-25 2012-03-09 Oreal Composition oxydante comprenant des composes insolubles, procedes mettant en oeuvre cette composition
FR2889945B1 (fr) 2005-08-25 2011-07-29 Oreal Composition de coloration directe comprenant des composes oxygenes insolubles, procedes mettant en oeuvre cette composition.
US7481847B2 (en) 2006-03-28 2009-01-27 L'oreal S.A. Dye composition comprising at least one cationic hydrazone direct dye, dyeing process, and multi-compartment devices
FR2901126B1 (fr) 2006-05-22 2012-08-31 Oreal Utilisation d'un hydrotrope anionique pour la coloration de fibres keratiniques, composition le comprenant et procedes de coloration la mettant en oeuvre
FR2901127B1 (fr) 2006-05-22 2012-08-31 Oreal Utilisation d'un hydrotrope cationique pour la coloration de fibres keratiniques, composition le comprenant et procedes de coloration la mettant en oeuvre
FR2917737B1 (fr) 2007-06-22 2012-06-01 Oreal Composition de coloration comprenant un compose de type azomethinique a motif pyrazolinone
FR2925307B1 (fr) 2007-12-21 2009-12-18 Oreal Procede de coloration directe eclaircissante ou d'oxydation en presence d'une amine organique particuliere et dispositif
FR2925323B1 (fr) 2007-12-21 2009-12-18 Oreal Procede de coloration en presence d'un agent oxydant et d'une amine organique particuliere et dispositif
FR2929110B1 (fr) 2008-03-28 2010-04-16 Oreal Dispersion aqueuse oxydante pour le traitement des fibres keratiniques comprenant un compose amphiphile non ionique a caractere hydrophobe
FR2940077B1 (fr) 2008-12-19 2012-07-20 Oreal Procede de coloration eclaircissante de matieres keratiniques mettant en oeuvre une composition anhydre colorante comprenant un agent alcalin et une composition oxydante.
FR2940067B1 (fr) 2008-12-19 2011-02-25 Oreal Composition oxydante pour le traitement des fibres keratiniques comprenant un polymere cationique, un amide gras et un agent-oxygene
US7922777B2 (en) 2008-12-19 2011-04-12 L'ORéAL S.A. Lightening and dyeing of human keratin fibers using an anhydrous composition comprising a monoethyanolamine/basic amino acid mixture, and device therefor
BRPI0906138A2 (pt) 2008-12-19 2013-04-09 Oreal processo de coloraÇço das fibras queratÍnicas humanas, processo de clareamento das fibras queratÍnicas humanas e dispositivo com vÁrios compartimentos
FR2940090B1 (fr) 2008-12-19 2011-02-25 Oreal Composition oxydante pour le traitement des fibres keratiniques comprenant une huile, un alcool gras et un alcool gras oxyalkylene
FR2940103B1 (fr) 2008-12-19 2011-06-10 Oreal Procede de coloration eclaircissante de matieres keratiniques mettant en oeuvre une emulsion comprenant un colorant et un agent alcalin et une composition oxydante
JP5748953B2 (ja) 2008-12-19 2015-07-15 ロレアル 無水組成物およびモノエタノールアミン／塩基性アミノ酸混合物を使用して、ヒトのケラチン繊維を染色または明色化するための方法、ならびにそのための適切なデバイス
US7935154B2 (en) 2008-12-19 2011-05-03 L'oreal S.A. Process for lightening or lightening direct dyeing or oxidation dyeing in the presence of at least one organic amine and at least one inorganic base, and device therefor
JP5711883B2 (ja) 2008-12-19 2015-05-07 ロレアル 脂肪物質に富む水性組成物の存在下で、淡色化し、あるいは淡色化直接染色し、あるいは酸化染色する方法、及びそのためのデバイス
BRPI0907294A2 (pt) 2008-12-19 2013-05-07 Oreal processo de clareamento ou de coloraÇço das fibras queratÍnicas e dispositivo com vÁrios compartimentos
FR2940104B1 (fr) 2008-12-19 2011-08-19 Oreal Procede de traitement des cheveux mettant en oeuvre une emulsion directe comprenant un agent oxydant et une composition contenant un agent alcalin
FR2942704B1 (fr) 2009-03-04 2011-09-02 Oreal Dispositif de distribution d'une composition tinctoriale pour les fibres keratiniques et procede associe.
FR2945041B1 (fr) 2009-04-30 2011-04-08 Oreal Composes de type azomethinique a motif pyrazolopyridine cationique pour la coloration des fibres keratiniques
FR2944959B1 (fr) 2009-04-30 2011-04-08 Oreal Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine
FR2949971B1 (fr) 2009-09-17 2012-08-17 Oreal Procede d'eclaircissement ou de coloration en presence d'une composition anhydre particuliere et dispositif
FR2951080B1 (fr) 2009-10-13 2012-01-20 Oreal Composition comprenant un corps gras et un acide organophosphonique ou l'un de ses sels, procede de coloration ou d'eclaircissement la mettant en oeuvre et dispositifs
FR2954121B1 (fr) 2009-12-22 2016-03-25 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties, comprenant un corps gras particulier et une reductone.
FR2954127B1 (fr) 2009-12-22 2015-10-30 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties, comprenant un corps gras et un agent sequestrant.
FR2954160B1 (fr) 2009-12-22 2012-03-30 Oreal Composition de coloration ou d'eclaircissement comprenant un corps gras et un polymere amphotere
WO2011076646A2 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratin fibres, comprising an inverse emulsion comprising an oxidizing agent
FR2954101B1 (fr) 2009-12-22 2012-05-11 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties ou plus, comprenant une composition alcaline en emulsion inverse.
FR2954093B1 (fr) 2009-12-22 2012-02-24 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties ou plus sous forme d'emulsion et de dispersion
EP2515831A2 (en) 2009-12-22 2012-10-31 L'Oréal Inverse emulsion for treating the hair comprising a particular fatty substance and an alkaline agent
FR2954113B1 (fr) 2009-12-22 2013-03-08 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties ou plus, sous forme d'emulsion.
FR2954161B1 (fr) 2009-12-23 2012-03-02 Oreal Procede de coloration ou d'eclaircissement de fibres keratiniques en presence d'alcane(s) lineaire(s) volatil(s) et dispositif
FR2958161B1 (fr) 2010-04-02 2012-04-27 Oreal Procede de traitement des cheveux mettant en oeuvre une emulsion directe comprenant un agent oxydant et une emulsion directe contenant un agent alcalin
FR2959127B1 (fr) 2010-04-22 2016-01-01 Oreal Emulsion inverse pour le traitement des cheveux comprenant un solvant particulier
FR2960773B1 (fr) 2010-06-03 2015-12-11 Oreal Procedes de traitement cosmetique utilisant un revetement a base d'un polymere polyamide-polyether
WO2015063122A1 (en) 2013-10-30 2015-05-07 L'oreal Expanded dyeing composition comprising an inert gas, an oxidation dye and an oxyalkylenated nonionic surfactant
FR3030246B1 (fr) 2014-12-19 2017-02-10 Oreal Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine
FR3030522B1 (fr) 2014-12-19 2017-02-10 Oreal Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a deux motifs pyrazolopyridines
FR3037795B1 (fr) 2015-06-25 2018-08-17 L'oreal Article de conditionnement comportant une enveloppe et une composition colorante, decolorante ou oxydante anhydre comprenant une argile fibreuse, et un compose choisi parmi un agent colorant et/ou un agent oxydant ; utilisation et procede pour colorer et/ou decolorer les fibres keratiniques
BR112018012065B8 (pt) 2015-12-18 2022-01-04 Oreal Composição para tratamento de materiais de queratina e processo para tratamento, tingimento e/ou clareamento
FR3045331B1 (fr) 2015-12-21 2019-09-06 L'oreal Composition de coloration a ph acide comprenant un colorant direct de structure triarylmethane
FR3045346B1 (fr) 2015-12-21 2019-08-30 L'oreal Composition de coloration comprenant un colorant direct de structure triarylmethane, et une silicone
FR3052970B1 (fr) 2016-06-23 2018-06-29 L'oreal Procede de traitement des fibres keratiniques mettant en œuvre une composition anhydre comprenant un compose de type azomethinique a deux motifs pyrazolopyridines et une composition aqueuse
FR3052969B1 (fr) 2016-06-23 2020-02-21 L'oreal Utilisation pour la coloration des fibres keratiniques d’un compose de type azomethinique a motif derive de quinoline
FR3053041A1 (fr) 2016-06-23 2017-12-29 Oreal Colorant direct de type azomethinique (dis)symetrique comprenant au moins un motif pyrazolopyridine, procede de coloration des fibres keratiniques a partir de ce colorant
FR3059233B1 (fr) 2016-11-28 2019-07-26 L'oreal Composition tinctoriale comprenant l'acide 12-hydroxystearique, une amine organique et un colorant
FR3082119B1 (fr) 2018-06-06 2020-05-15 L'oreal Procede de coloration et/ou d’eclaircissement des matieres keratiniques
FR3090345B1 (fr) * 2018-12-21 2021-06-25 Oreal Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel ammonium aliphatique et composition les comprenant
FR3097761B1 (fr) 2019-06-27 2021-05-28 Oreal Composition comprenant l’acide 12-hydroxystéarique, une amine organique et un corps gras liquide
US20230065360A1 (en) 2019-12-24 2023-03-02 L'oreal Cosmetic composition comprising a polymer comprising at least one cationic (meth)acrylamide unit, a particular silicone and at least one surfactant
FR3113240B1 (fr) 2020-08-10 2024-01-12 Oreal Composition comprenant au moins un silicone particulier, au moins un alcane et au moins une teinte directe et/ou au moins un pigment

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3100739A (en) * 1958-02-25 1963-08-13 Therachemie Chem Therapeut Process for dyeing human hair with water soluble, quaternary ammonium containing dyes
US3912708A (en) * 1970-07-27 1975-10-14 Du Pont Biscationic pyridinium monoazo dyes useful for dyeing acid-modified nylons
EP0482508A1 (de) * 1990-10-26 1992-04-29 BASF Aktiengesellschaft Biskationische Azofarbstoffe sowie deren Zwischenprodukte
FR2741798A1 (fr) * 1995-12-01 1997-06-06 Oreal Composition de teinture eclaircissante pour fibres keratiniques comprenant un colorant direct specifique

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE626050A (es) 1962-03-30
US3271383A (en) * 1963-06-11 1966-09-06 Mitsubishi Chem Ind Disazo dyes containing an nu-substituted benzothiazolyl group
DE1492175A1 (de) 1965-07-07 1970-02-12 Schwarzkopf Gmbh Hans Verfahren zum Faerben von lebenden Haaren
US3291788A (en) * 1965-09-27 1966-12-13 Mitsubishi Chem Ind Cationic triazole disazo dyestuffs
CH468188A (fr) * 1966-02-15 1969-02-15 Oreal Procédé de teinture décolorante pour cheveux et composition tinctoriale pour la mise en oeuvre dudit procédé
GB1186753A (en) 1966-07-16 1970-04-02 Sumitomo Chemical Co New Basic Disazo Dyes and a process for their preparation
DE2359399C3 (de) 1973-11-29 1979-01-25 Henkel Kgaa, 4000 Duesseldorf Haarfärbemittel
US4003699A (en) * 1974-11-22 1977-01-18 Henkel & Cie G.M.B.H. Oxidation hair dyes based upon tetraaminopyrimidine developers
JPS5522638A (en) 1978-08-03 1980-02-18 Haruo Yamaguchi Hairdye
JP2526099B2 (ja) 1988-07-07 1996-08-21 花王株式会社 角質繊維染色組成物
DE3843892A1 (de) * 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
DE4133957A1 (de) * 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
JP3053939B2 (ja) 1991-12-17 2000-06-19 花王株式会社 角質繊維染色組成物
DE4234885A1 (de) 1992-10-16 1994-04-21 Wella Ag Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten, deren Verwendung zum Färben von Haaren sowie neue Pyrazol-Derivate
DE4234887A1 (de) 1992-10-16 1994-04-21 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung
TW311089B (es) 1993-07-05 1997-07-21 Ciba Sc Holding Ag
TW325998B (en) 1993-11-30 1998-02-01 Ciba Sc Holding Ag Dyeing keratin-containing fibers
ES2215944T3 (es) * 1994-11-03 2004-10-16 Ciba Specialty Chemicals Holding Inc. Colorantes imidazolazoicos cationicos.
DE4440957A1 (de) 1994-11-17 1996-05-23 Henkel Kgaa Oxidationsfärbemittel
FR2733749B1 (fr) 1995-05-05 1997-06-13 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0757083A3 (de) 1995-08-02 2000-01-12 Ciba SC Holding AG Kationische Thiazolazu- und Benzthiazolazofarbstoffe
DE19539264C2 (de) 1995-10-21 1998-04-09 Goldwell Gmbh Haarfärbemittel
DE19543988A1 (de) * 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3100739A (en) * 1958-02-25 1963-08-13 Therachemie Chem Therapeut Process for dyeing human hair with water soluble, quaternary ammonium containing dyes
US3912708A (en) * 1970-07-27 1975-10-14 Du Pont Biscationic pyridinium monoazo dyes useful for dyeing acid-modified nylons
EP0482508A1 (de) * 1990-10-26 1992-04-29 BASF Aktiengesellschaft Biskationische Azofarbstoffe sowie deren Zwischenprodukte
FR2741798A1 (fr) * 1995-12-01 1997-06-06 Oreal Composition de teinture eclaircissante pour fibres keratiniques comprenant un colorant direct specifique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
H. GOTTHARDT ET AL: "Neue elektrophile Substitutionen und 1,4-Dipolare Cycloadditionen in der Pyrimidinium-4-olat-Reihe", CHEMISCHE BERICHTE., vol. 118, 1985, WEINHEIM DE, pages 4578 - 4587, XP002192635 *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006525977A (ja) * 2003-05-09 2006-11-16 ロレアル 熱を加えることによりケラチン繊維をトリートメントするための方法
JP2006348264A (ja) * 2004-10-14 2006-12-28 L'oreal Sa ジカチオンビス−ヒドラゾン化合物、少なくとも一種のこのような化合物を含む染料組成物、その実施方法及びその使用
WO2006056489A2 (en) * 2004-11-26 2006-06-01 L'oreal Particular dissymmetrical cationic polyazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibres and device therefor
FR2878527A1 (fr) * 2004-11-26 2006-06-02 Oreal Composes polyazoiques cationiques dissymetriques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif
WO2006056489A3 (en) * 2004-11-26 2006-10-19 Oreal Particular dissymmetrical cationic polyazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibres and device therefor
FR2879191A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques particuliers et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
WO2006063869A3 (en) * 2004-12-15 2006-08-03 Oreal Symmetrical diazo compounds with 3-pyridinium groups and cationic linker arm, compositions comprising same, dyeing method and device
FR2879195A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
EP1671954A1 (fr) * 2004-12-15 2006-06-21 L'oreal Composés diazoiques présentant un motif 2-imidazolium et leur utilisation dans des compositions tinctoriales
EP1671952A1 (fr) * 2004-12-15 2006-06-21 L'oreal Composes diazoiques dissymetriques et leur utilisation dans des compositions tinctoriales
WO2006063866A1 (fr) * 2004-12-15 2006-06-22 L'oréal Composes diazoiques dissymetriques, compositions les comprenant, procede de coloration et dispositif renfermant ces compositions
WO2006063869A2 (en) * 2004-12-15 2006-06-22 L'oreal Symmetrical diazo compounds with 3-pyridinium groups and cationic linker arm, compositions comprising same, dyeing method and device
WO2006063867A2 (en) * 2004-12-15 2006-06-22 L'oréal Symmetrical diazo compounds containing 3-pyridinium groups and a non-cationic linker, compositions comrisisng them, method of colouring, and device
EP1672033A3 (fr) * 2004-12-15 2006-07-19 L'oreal Composés diazoiques symetriques à groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procédé de coloration et dispositif
FR2879198A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 3-pyridium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif
WO2006063867A3 (en) * 2004-12-15 2006-08-03 Oreal Symmetrical diazo compounds containing 3-pyridinium groups and a non-cationic linker, compositions comrisisng them, method of colouring, and device
FR2879193A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques presentant au moins un motif 2-imidazolium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
FR2879197A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques symetriques a groupements 3-pyridinium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif
FR2879190A1 (fr) * 2004-12-15 2006-06-16 Oreal Composes diazoiques dissymetriques presentant au moins un motif 4-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
US7247713B2 (en) 2004-12-15 2007-07-24 L'oreal, S.A. Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device
US7288639B2 (en) 2004-12-15 2007-10-30 L'oreal S.A. Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device
US7351267B2 (en) 2004-12-15 2008-04-01 L'oreal S.A. Symmetrical diazo compounds comprising 2-imidazolium groups and a non-cationic linke, compositions comprising them, method of coloring, and device
US7396368B2 (en) 2004-12-15 2008-07-08 L'oreal S.A. Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device
US7438728B2 (en) 2004-12-15 2008-10-21 L'oreal S.A. Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device

Also Published As

Publication number Publication date
PT1399117E (pt) 2007-02-28
EP1399117A1 (fr) 2004-03-24
FR2825702B1 (fr) 2003-08-08
CN1541086A (zh) 2004-10-27
JP2005516887A (ja) 2005-06-09
US6893471B2 (en) 2005-05-17
EP1399117B1 (fr) 2006-11-02
DE60215808D1 (de) 2006-12-14
ES2274077T3 (es) 2007-05-16
KR20040003065A (ko) 2004-01-07
BR0210997A (pt) 2004-06-08
DE60215808T2 (de) 2007-08-30
ATE344090T1 (de) 2006-11-15
US20040143911A1 (en) 2004-07-29
MXPA03011393A (es) 2004-04-05
FR2825702A1 (fr) 2002-12-13
CN1277528C (zh) 2006-10-04

Similar Documents

Publication Publication Date Title
WO2002100368A1 (fr) Composition pour la teinture des fibres keratiniques comprenant un colorant diazo'ique dicationique particulier
EP1416909A2 (fr) Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier
WO2002100834A1 (fr) Composition pour la teinture des fibres keratiniques comprenant un colorant diazoïque dicationique particulier
EP1377265B1 (fr) Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoique cationique
EP1398355A1 (fr) Composition pour la teinture des fibres kératiniques humaines comprenant un colorant monoazoique monocationique
EP1297819A2 (fr) Composition pour la teinture des fibres kératiniques comprenant un colorant azoique cationique particulier
WO2002078596A2 (fr) Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier
WO2002078658A1 (fr) Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoïque cationique
WO2002080869A2 (fr) Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique particulier
WO2002078657A1 (fr) Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoïque cationique
EP1377264A1 (fr) Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoique cationique
EP1637566A1 (fr) Composés diazoiques cationiques, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif
EP1634926A1 (fr) Composés diazoiques cationiques particuliers, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif
FR2879195A1 (fr) Composes diazoiques symetriques a groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif
EP1679312A2 (fr) Composés diazoiques symetriques à groupements 2-imidazolium et bras de liaison cationique, compositions les comprenant, procédé de coloration et dispositif
EP1619220A1 (fr) Composes diazoiques cationiques particuliers, compositions les comprenant à titre de colorant direct, procédé de coloration de fibres kératiniques et dispositif
EP1757264A2 (fr) Colorants azoïques cationiques à motifs julolidine composition tinctoriale les contenant procédé de coloration
EP1859784B1 (fr) Utilisation d`un hydrotrope cationique pour la coloration de fibres kératiniques, composition le comprenant et procédés de coloration la mettant en oeuvre
FR2878527A1 (fr) Composes polyazoiques cationiques dissymetriques particuliers, compositions les comprenant a titre de colorant direct, procede de coloration de fibres keratiniques et dispositif
FR2879198A1 (fr) Composes diazoiques symetriques a groupements 3-pyridium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif
FR2879197A1 (fr) Composes diazoiques symetriques a groupements 3-pyridinium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif
FR3053041A1 (fr) Colorant direct de type azomethinique (dis)symetrique comprenant au moins un motif pyrazolopyridine, procede de coloration des fibres keratiniques a partir de ce colorant
WO2007122341A2 (fr) Composes monochromophoriques monocationiques particuliers de type hydrazone comprenant un motif 2-(benz-)imidazolium, leur synthese, compositions tinctoriales les comprenant, procede de coloration de fibres keratiniques
FR2899898A1 (fr) Composes monochromophoriques monocationiques particuliers de type hydrazone comprenant un motif 2-(benz-) imidazolium leur synthe, compositions tinctoriales les comprenant, procede de coloration de fibres keratiniques
WO2007125238A1 (fr) Composes monochromophoriques monocationiques particuliers de type hydrazone comprenant un motif 2-, 4-pyridinium ou 2-, 4-quinolinium, leur synthese, compositions tinctoriales les comprenant, procede de coloration de fibres keratiniques

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2002760357

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: PA/a/2003/011393

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 2003503192

Country of ref document: JP

Ref document number: 1020037016170

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 20028157524

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 10480153

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2002760357

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 2002760357

Country of ref document: EP